This article argues that in pluralistic, secular, democratic schooling we need a concept of critical character education. There are substantial challenges to the theory and practice of character education, which indicates that character education is a "problem" in the philosophical sense. The way forward is to cultivate a critical theory of character education, which is democratic, culturally responsive, socially relevant, and philosophical complex. This understanding of character and virtue as a problem is grounded in the philosophical tradition from Socrates to Alasdair MacIntyre. The theory of education grounding the idea of critical character education is found in sources such as Dewey, Freire, and Noddings. As we confront global challenges to democracy, the way forward must include a theory of critical character education.